Justice for All: Meet the New Leadership at Pro Bono SG
In the heart of Singapore’s legal aid landscape, Pro Bono SG has established itself as a cornerstone institution ensuring access to justice for the most vulnerable members of society. This April marks a significant milestone in the organisation’s journey with the appointment of two remarkable women to key inaugural leadership positions: Sadhana Rai as Chief Representation Officer and Cai Chengying as Deputy Chief Executive Officer.
Their promotions represent more than just career advancement; they signal a new chapter for Pro Bono SG under the stewardship of legal professionals whose personal journeys, professional excellence, and unwavering commitment to justice have defined their careers. We sat down with these two leaders to understand the women behind the titles, their vision for Pro Bono SG, and what justice for all truly means in practice.
Paths Converging on Purpose
Both Sadhana Rai and Cai Chengying found their way to Pro Bono SG in 2015, but their journeys to that point were distinctly personal.
Guided at an early age by an instinct to speak up for what she believed in, Sadhana’s legal career began at Drew & Napier LLC, where she sharpened her litigation skills under the tutelage of Senior Counsel Davinder Singh. While she found private practice exhilarating in its own way, her heart tugged her elsewhere. In 2015, she joined Pro Bono SG as part of the pioneer batch of Criminal Legal Aid Scheme (CLAS) Fellows, marking the start of a decade-long odyssey in pro bono work. “From a young age, I found myself drawn to advocacy,” she shared during the cross-interview. “I was naturally inclined to speak up on issues of justice – it was important to me to argue for what felt right”. This instinct, combined with a desire to find greater meaning in her work, eventually led her to Pro Bono SG. “A legal education is a privilege, and to be able to give back holds deep personal meaning to me. It is very fulfilling to be able to give of myself and my skills to those who need it — without the weight of other demands” she reflects. What started as a fellowship grew into a decade-long commitment that has seen her represent over 500 clients in criminal matters, appearing at all levels of Singapore courts.
Cai Chengying’s journey reflects a different but equally purposeful trajectory. From a young age, she envisioned a career in a helping profession, believing that law offered a powerful means to give back. Her journey, however, was not without its initial setbacks. During her undergraduate years at the National University of Singapore (NUS) Law, her attempt to join the Pro Bono Club was unsuccessful. Undeterred, she joined the Law Club as the Academic Secretary, gaining valuable insights into the practical aspects of law. In 2015, she was seconded by her employer Allen & Gledhill LLP to serve as a pioneer CLAS Fellow, dedicating herself to full-time pro bono criminal defence work.
After her fellowship, Chengying returned to private practice and later took time to focus on her family. Her decision to rejoin Pro Bono SG five years ago came from a place of deep reflection: “If I wanted to spend time away from my family, I wanted to come back to something that I absolutely believed in and found meaning in and would not regret spending time on.”
Redefining Access to Justice
Both leaders have evolved in their understanding of access to justice throughout their careers at Pro Bono SG. What began as a lawyer-centric view has transformed into a holistic, user-centred approach.
“When I first came to Pro Bono SG, it was in the capacity of a volunteer lawyer, and I viewed access to justice really from my lens,” Chengying explains. “My approach to access to justice was from that limited, single perspective.”
Her work launching Community Law Centres fundamentally changed this outlook. “Access to justice is really the client, the service user, at the centre of it, and all the decisions that we make should also surround that person. Access is more than just giving them a lawyer. It’s about how is that nature of that service — is it dignified? Is it helpful? Is it compassionate and is it empowering?”
Sadhana reflects on her own evolving understanding of access: “Like Chengying, when I first began, I saw access in very binary terms. It was simply about getting a lawyer and receiving legal services.” However, as time passed, she began to understand the deeper, more nuanced barriers that individuals face — even in situations where legal professionals might take basic access for granted. “My view of access has grown more complex over time,” she explains. “It’s not just about physical resources like our Help Centre. We need to ask: Is it truly accessible? Our clients often face financial, emotional, mental, and even physical barriers to accessing legal support. The challenges they face are far broader, and to truly address them, we must approach these issues with compassion, recognising the many layers that impact access.”
This sophisticated understanding of access has guided their approach to leadership, shaping Pro Bono SG’s services to be more responsive to the multifaceted needs of vulnerable populations.
The Community Lawyering Movement
One of the most transformative initiatives under their leadership has been the establishment of Community Law Centres, bringing legal services directly into heartland locations. As Head of Community Lawyering, Chengying spearheaded the launch of the first centre at Tian De Temple in Hougang, followed by a second centre in Woodlands and the Transnational Family Care Centre.
Interestingly, she initially had reservations about the concept. “When the idea was first shared with me — let’s set up a branch office in the heartlands, let’s go to a place of worship to conduct the services — I had so many doubts,” she admits. “I argued with Tanguy [the CEO] for some time about it.”
Her concerns centred on consolidating existing services before expanding. “Instead of kind of perfecting what we’re doing in the State Courts, why are we starting something new?” Yet the impact of these centres quickly proved their value, with the first centre assisting nearly 1,000 clients in its initial year of operation.
The centres, staffed by community lawyers from Sadhana’s team, address crucial barriers to access, particularly for those facing challenges related to mobility, technology, and social exclusion. Chengying’s vision now extends to establishing five community law centres across Singapore, further embedding legal services within the fabric of local communities.
Leading Through Challenge and Change
The leadership styles of both women reflect their personal journeys and a shared commitment to person-centred justice.
For Sadhana, who has navigated the male-dominated field of criminal law, leadership is about inspiring her team while keeping service users at the centre of everything: “For my team, the service user is at the centre of everything we do, and it is about making life a lot easier for the human being that is coming through our doors.”
Chengying’s leadership philosophy emphasises connecting people to resources and needs. “My favourite part of the job is really connecting people to where the needs are,” she shares. Whether linking donors with initiatives or volunteers with opportunities, she finds deep satisfaction in facilitating these connections.
Both leaders acknowledge the emotional challenges inherent in their work. Cases often involve individuals facing serious charges, dire circumstances, and systemic barriers.
Female Leadership in Law: Breaking Barriers
As women in leadership positions within the legal profession, both Sadhana and Chengying have faced unique challenges. Their experiences offer valuable insights into navigating gender-based assumptions and building credibility in traditionally male-dominated spaces.
Sadhana, particularly in her criminal law practice, has encountered skepticism from male clients. “Taking instructions from male clients can be very difficult because some of them just will not trust you, and will prefer a male lawyer,'” she explains. “But once they see you perform in court, and they see you advocating fiercely for them, all these considerations fall away.”
She also points to the different manifestations of advocacy for women versus men — from voice modulation to facial expressions — noting that female advocates must navigate additional expectations.
Chengying recalls a moment early in her CLAS career when a client looked at her and asked, “Xiaomei, are you really my lawyer?” The experience prompted self-doubt: “Should I have carried myself differently? Should I have dressed up more? Should I have tried to look a bit more mature?”
Over time, both have learned to respond to these challenges with confidence and perspective. “People react that way because when they come to us, they’re just so anxious,” Chengying reflects. “We do have a duty to put them at ease and make them feel comfortable, and we do have to earn their trust.”
Their success in building credibility and advancing to senior leadership positions serves as an inspiration for the next generation of women in law.
Sustaining the Culture of Service
A remarkable aspect of Pro Bono SG is its organisational culture, which has attracted and retained passionate advocates like Sadhana, who has remained with the organisation for a decade.
When asked what has kept her there, Sadhana points to two critical factors: “Good leadership is critical. I have a leader who I believe in, and who understood how to engage the best of me. Every year, I was given a new challenge, and new opportunities to grow. I felt that the leadership here understood what it took to keep the fire in me burning.”
The second factor is the organisation’s strong value system. “We’re all driven by something very similar, which is a sense of purpose,” she explains. “Without that sense of purpose, people have very little reason to stay.”
This culture of purpose and growth has fostered loyalty not just from Sadhana and Chengying, but from many who have passed through Pro Bono SG’s doors. As Sadhana notes, “People who leave always try to come back. For some reason, this is the place that they felt most fulfilled.”
Looking Ahead: Vision for Pro Bono SG
As they step into their new roles, both leaders bring clear visions for the future of Pro Bono SG.
Chengying emphasises sustainability — both financial and in terms of relevance. “We have inherited a really important legacy, something that has been built on collectively, by the bar, by the general public, by other supporters, over generations,” she reflects. Keeping “a finger on the pulse” of changing community needs is central to her approach.
Sadhana envisions what she playfully calls “a Pro Bono Empire filled with Pro Bono lawyers or warriors” — a next generation of lawyers who recognise the value of their contributions to society. She also aspires to eliminate silos in service delivery: “It shouldn’t be so difficult to get help. You should be able to come to someone and say, ‘Hey, I need help with this,’ and be directed to the right place.”
The Goodness in People
Perhaps the most profound discovery both leaders have made through their work is the inherent goodness in people — particularly within the legal profession.
Sadhana shares a moving story about preparing submissions for an unprecedented application to have a deceased candidate called to the Bar posthumously. When they reached out to international law firms for help finding relevant precedents, the response was immediate and overwhelming.
“In my mind, I’m just thinking, what is going on? Why are people so good? Why do they want to help a complete stranger who isn’t even around to thank them anymore?” she recalls. “It was that day that I learned that when there’s a cause that people truly care about, they will give of themselves, and they will give from their hearts.”
This experience transformed her outlook. “Even today, when I look at the number of volunteers who take up cases with us and give their best to those in need, it reinforces my faith. I see a lot of goodness in our lawyers, and in our volunteers, and I am very proud to be a part of this profession.”
Justice for All
As Pro Bono SG enters this new chapter under Sadhana Rai and Cai Chengying’s leadership, their personal dedication, professional excellence, and shared vision promise to further strengthen the organisation’s vital work.
Their stories illuminate not just individual career achievements, but a profound commitment to the principle that justice should not be a privilege for those who can afford it, but a right accessible to all. Through their innovative approaches, strategic thinking, and deep empathy, they are reshaping what access to justice means in Singapore — making it more human-centred, community-embedded, and responsive to the complex needs of vulnerable populations.
In a profession often defined by its traditions, Sadhana Rai and Cai Chengying stand as powerful examples of how compassionate leadership and unwavering purpose can transform institutions and lives. As they lead Pro Bono SG forward, their impact extends beyond the organisation itself, inspiring a more inclusive and equitable vision of justice for Singapore.
